芴苯聚合物的合成、光物理性能、聚集态结构及相互关系研究
摘要
有机聚合物材料在光电方面的应用开拓了一个全新的信息功能材料及其器件的研究开发领域，在全世界引起了越来越多人的重视。在各种有机聚合物材料当中，聚芴及其衍生物由于具有宽的能隙、高的发光效率等特点引起了广泛的研究，并被认为是最具商业应用前景的蓝光材料之一。目前，关于聚芴及其衍生物的研究大多集中在新型结构材料的开发领域，而对于材料的结构尤其是聚集态结构与光物理性能之间关系的研究尚处于起步阶段，详细而系统地研究此类材料的结构与性能之间的关系无疑对新材料的开发以及高性能器件的制备具有十分重要的理论意义和实践价值。因此，本论文设计合成了一系列含芴苯结构的发光聚合物，同时通过各种表征手段详细研究了所制备的系列聚合物分子设计-聚集态结构-光电等物理性能之间的关系，并得到了一些非常有意义的研究结果。
一、通过合理的分子设计并采用Suzuki偶联聚合的方法合成了一系列化学结构明确、侧基性质(长度、体积、给吸电子性质)不同、主链共轭的Hairy-rod型芴苯共聚物。通过光谱、电化学和模拟计算等手段研究了苯环上不同性质的侧基取代芴苯聚合物的发光性质、电化学性质和溶剂化效应等，同时研究了侧基性质的变化对这些物理性质的影响规律。苯环上烷基侧链长度的改变对取代共聚物的光谱、电化学和发光效率等影响很小；而随着苯环上烷氧基侧链长度的增加，聚合物的光谱稳定性逐渐增强，荧光发射光谱中的0-1转变逐渐被抑制，荧光发射半峰宽减小。苯环上取代侧基的给吸电子性质变化对聚合物的光电性能具有全面的影响，改变取代侧基的给吸电子性质可调节芴苯共聚物的发光颜色和HOMO、LUMO能级以及HOMO-LUMO能隙等，因此，通过引入不同性质的侧基可以实现对此类聚合物光物理性能的调控。溶剂的极性对聚合物溶液的光谱性能有显著的影响，溶液光谱随溶剂极性的增大逐渐向长波移动。当聚合物本身带有强极性基团时，在强极性溶剂中将发生聚合物分子链与溶剂分子间的强极性相互作用，从而导致或引起更复杂的结果。
二、通过薄膜退火实验研究了聚合物的光谱稳定性。苯环上未取代聚合物PF6P的薄膜在空气中退火后在长波(515 nm)出现一个新的荧光发射峰，随退火温度的升高或退火时间的延长，该长波荧光发射峰的强度逐渐增大，薄膜的紫外吸收峰变宽。苯环上烷基、烷氧基取代的聚合物则具有优异的光谱热稳定性能，其在空气退火的薄膜没有出现低能的长波发射。通过红外光谱和瞬态荧光等测试手段以及对比实验进一步研究了PF6P空气退火薄膜长波发射的来源。一方面，未取代的PF6P薄膜和烷氧基取代苯的PF60C6薄膜在空气中退火后都产生了芴酮结构，随退火温度的升高所生成的芴酮结构的含量逐渐增大；另一方面，新的长波发射随退火温度的升高其荧光寿命明显增加，因此确定PF6P空气退火薄膜的长波发射是来源于芴酮的激基缔合物。
三、通过X-射线衍射(XRD)、示差扫描量热仪(DSC)和形貌表征等手段研究了苯环上取代基烷基、烷氧基长度对聚合物形貌、相转变过程等的影响。苯环上烷基、烷氧基取代的聚合物都具有纤维状的特征形貌，当烷基、烷氧基碳原子数为6时在高温都存在一个向列液晶相，当烷基碳原子数增加到10时液晶相消失，而烷氧基碳原子数增加到12时该向列液晶相仍然存在。苯环上烷氧基取代的聚合物能自组装形成一种层状结构，其相转变行为具有明显的烷氧基链长依赖性。烷氧基碳原子数为6时，聚合物(PF60C6)具有一个稳定的结晶相C1和一个不稳定的结晶相C2，当烷氧基长度增加后，PF60C8等均只有一个结晶相；存DSC升温曲线上PF60C8具有多重熔融行为，而随烷氧基长度的继续增加，多重熔融现象逐渐被抑制，在PF60C12中被完全抑制而消失。苯环上烷氧基取代的聚合物薄膜的荧光发射光谱与薄膜形貌密切相关，薄膜的有序性增大，0-1转变减小。
四、通过DSC研究了聚合物PF60C10和PF60C12的非等温熔体结晶行为以及PF60C10分子量对非等温结晶和结晶后熔融行为的影响。Ozawa方程和Avrami方程在描述聚合物PF60C10和PF60C12的非等温熔体结晶过程时均有一定的局限性，而用Avrami和Ozawa联合的方法能有效地处理该非等温结晶动力学过程。PF60C10的结晶速率随分子量的增加而增大，PF60C12由于侧链长度增加使其分子链活动性减小，与PF60C10相比其结晶速率减小。另外，分别用Kissinger，Takhor和Augis-Bennett三种模型对PF60C10和PF60C12的非等温结晶活化能进行了估算。PF60C10经非等温结晶后的熔融行为具有明显的预冷速率和分子量依赖性，在一定分子量范围内在其DSC升温曲线上出现双重熔融现象，随着分子量的增大此双重熔融行为逐渐被抑制。
五、通过分子设计并采用Suzuki偶联聚合的方法合成了一系列主链结构刚柔交替的Rod-coil型芴苯聚合物，并对这类聚合物的光物理性能及相转变行为等进行了初步的探索性研究。主链中柔性链段长度的变化对聚合物的光物理性能没有明显的影响，而随主链中共轭链段长度的增加，聚合物光谱向长波移动，氧化电位逐渐增大，还原电位逐渐降低，HOMO-LUMO能隙增大。该Rod-coil型芴苯聚合物玻璃化转变温度随主链中柔性链段比例的增大而减小。聚合物P1(PF6P4P)在较低温度形成一种具有条带织构的液晶相，在DSC曲线的高温区具有典型的双重熔融行为。
Organic polymer materials have attracted much attention in the past decade because of their potential applications in light emitting diodes, field-effect transistors, photovoltaic cells, non-linear optical materials, and electrochromic devices. Among these polymers, fiuorene-based polymers are a kind of most promising blue-light-emitting materials for commercial applications due to their excellent properties such as high photoluminescence (PL) efficiency, good processability and thermal stability. However, much research about polyfluorenes and fluorene-based derivatives is mainly focused on the synthesis of polymers with novel chemical structures, and the investigations on condensed state structure, photophysical properties and their relationship are surprisingly lacking. In fact, it is of great significance to in-depth understand the relationship between condensed state structure and photophysical properties, which can provide more insights into the design of novel optoelectronic polymers as well as the fabrication of high performance devices. In this work, a series of fluorene-benzene based polymers were thus designed and successfully synthesized, and the relationship of molecular structure-condensed state structure-photophysical properties of these polymers were investigated in detail by using various characterization techniques.
1. A series of so-called hairy-rod fluorene-alt-benzene based polymers with different substituted groups on phenylene were synthesized through Suzuki route. The optical properties, fluorescence quantum yields (QY) and electrochemical properties of these polymers were investigated. It was found that the optical properties of the polymers did not show obvious dependence on the alkyl length on phenylene. However, the spectral stability was increased, and the 0-1 transition and the full width at the half-maximum (fwhm) of photoluminescence (PL) spectra was decreased with the increase of the alkoxy length on phenylene. The nature (e.g. electron-donating and electron-withdrawing) of the substituted side groups on phenylene has obvious effect on the optical properties, QY and electrochemical properties of the polymers. Thus, the photophysical properties of the polymers can be tuned by attaching different substituted side groups onto the phenylene. The spectra of the polymers in solutions exhibit dependence on dielectric constants of the solvents used, and the spectra of the polymer solutions shift to longer wavelength with increasing the dielectric constants of the solvents.
2. The thermal stability of the spectra of the polymers was investigated by annealing experiments. A new emission peak located at long wavelength (at about 515 nm) appeared in PL spectra of the unsubstituted polymer (PF6P) films annealed in air, and the intensity of the long wavelength emission increased with the increase of annealing temperature or annealing time. However, the long wavelength emission did not appear in PL spectra of the polymers substituted with alkyl and alkoxy. By comparing the PL spectra of PF6P and the substituted polymers, Fourier-transform infrared (FTIR) Spectroscopy, and PL lifetime measurements have revealed that the long wavelength emission could be attributed to the formation of fluorenone-based excimers. Compared with PF6P, the attachment of alkyl or alkoxyl groups on phenylene effectively inhibits the formation of fluorenone-based excimers and thus remarkably improves the thermal stability of the spectra.
3. Morphology and phase behavior of the polymers substituted with alkyl and alkoxyl groups on phenylene were investigated by differential scanning calorimetry (DSC), X-ray diffraction (XRD) and other techniques. These polymers exhibit typical fibrillar morphology in the films. During heating in DSC, all the polymers substituted with alkoxy on phenylene show a nematic phase. The polymers substituted with hexyl and octyl on phenylene also show a nematic phase, however, the nematic phase disappears for the polymer substituted with decyl. The polymers substituted with alkoxy on phenylene self-organize into a lamellar structure, and their phase behavior shows obvious dependence on the alkoxy length. PF6OC6 shows two crystalline phases; further increasing the length of alkoxy, PF6OC8, PF6OC10 and PF6OC12 only show one crystalline phase. During heating in DSC, PF6OC8 exhibits a melting-recrystallization phenomenon, which is steadily inhibited as the length of alkoxy on phenylene increases. In addition, for the polymers substituted with alkoxy on phenylene, the 0-1 transition in PL spectra of the films decreases with the increase of ordered structure.
4. The nonisothermal crystallization kinetics of PF6OC10 and PF6OC12 was investigated by using differential scanning calorimetry (DSC) under different cooling rates from the melt. It was found that the Ozawa method failed to describe the nonisothermal crystallization behavior of the two polymers. Although the Avrami method did not effectively describe the nonisothermal crystallization kinetics of the two polymers for overall process, it was valid for describing the early stage of crystallization. The combined Avrami-Ozawa method proposed by Liu was able to satisfactorily describe the nonisothermal crystallization behavior of the two polymers. The crystallization activation energies determined by Kissinger, Takhor and Augis-Bennett models were comparable. The melting temperature of PF6OC10 increased with increasing molecular weight. For low molecular weight sample, PF6OC10 showed the characteristic of double melting phenomenon. The interval between the two melting peaks decreased with increasing molecular weight, and only one melting peak was observed for the high molecular weight sample.
5. A series of so-called rod-coil fluorene-benzene based polymers were synthesized through Suzuki coupled polymerization, and the photophysical properties and phase behavior of these polymers were investigated. The photophysical properties of the polymers did not show obvious dependence on the fraction of coil segments in backbone. However, with increasing the fraction of rod segments in backbone, the spectra of the polymers shift to long wavelength and the HOMO-LUMO energy gap increases. The glass transition temperature of the polymers steadily decreases with the increase of the fraction of coil segments in backbone. The polymer (P1(PF6P4P)) shows complex phase behavior, and a strip liquid crystalline texture is observed at low temperature and the typical double melting behavior can be observed at high temperature.
一、通过合理的分子设计并采用Suzuki偶联聚合的方法合成了一系列化学结构明确、侧基性质(长度、体积、给吸电子性质)不同、主链共轭的Hairy-rod型芴苯共聚物。通过光谱、电化学和模拟计算等手段研究了苯环上不同性质的侧基取代芴苯聚合物的发光性质、电化学性质和溶剂化效应等，同时研究了侧基性质的变化对这些物理性质的影响规律。苯环上烷基侧链长度的改变对取代共聚物的光谱、电化学和发光效率等影响很小；而随着苯环上烷氧基侧链长度的增加，聚合物的光谱稳定性逐渐增强，荧光发射光谱中的0-1转变逐渐被抑制，荧光发射半峰宽减小。苯环上取代侧基的给吸电子性质变化对聚合物的光电性能具有全面的影响，改变取代侧基的给吸电子性质可调节芴苯共聚物的发光颜色和HOMO、LUMO能级以及HOMO-LUMO能隙等，因此，通过引入不同性质的侧基可以实现对此类聚合物光物理性能的调控。溶剂的极性对聚合物溶液的光谱性能有显著的影响，溶液光谱随溶剂极性的增大逐渐向长波移动。当聚合物本身带有强极性基团时，在强极性溶剂中将发生聚合物分子链与溶剂分子间的强极性相互作用，从而导致或引起更复杂的结果。
二、通过薄膜退火实验研究了聚合物的光谱稳定性。苯环上未取代聚合物PF6P的薄膜在空气中退火后在长波(515 nm)出现一个新的荧光发射峰，随退火温度的升高或退火时间的延长，该长波荧光发射峰的强度逐渐增大，薄膜的紫外吸收峰变宽。苯环上烷基、烷氧基取代的聚合物则具有优异的光谱热稳定性能，其在空气退火的薄膜没有出现低能的长波发射。通过红外光谱和瞬态荧光等测试手段以及对比实验进一步研究了PF6P空气退火薄膜长波发射的来源。一方面，未取代的PF6P薄膜和烷氧基取代苯的PF60C6薄膜在空气中退火后都产生了芴酮结构，随退火温度的升高所生成的芴酮结构的含量逐渐增大；另一方面，新的长波发射随退火温度的升高其荧光寿命明显增加，因此确定PF6P空气退火薄膜的长波发射是来源于芴酮的激基缔合物。
三、通过X-射线衍射(XRD)、示差扫描量热仪(DSC)和形貌表征等手段研究了苯环上取代基烷基、烷氧基长度对聚合物形貌、相转变过程等的影响。苯环上烷基、烷氧基取代的聚合物都具有纤维状的特征形貌，当烷基、烷氧基碳原子数为6时在高温都存在一个向列液晶相，当烷基碳原子数增加到10时液晶相消失，而烷氧基碳原子数增加到12时该向列液晶相仍然存在。苯环上烷氧基取代的聚合物能自组装形成一种层状结构，其相转变行为具有明显的烷氧基链长依赖性。烷氧基碳原子数为6时，聚合物(PF60C6)具有一个稳定的结晶相C1和一个不稳定的结晶相C2，当烷氧基长度增加后，PF60C8等均只有一个结晶相；存DSC升温曲线上PF60C8具有多重熔融行为，而随烷氧基长度的继续增加，多重熔融现象逐渐被抑制，在PF60C12中被完全抑制而消失。苯环上烷氧基取代的聚合物薄膜的荧光发射光谱与薄膜形貌密切相关，薄膜的有序性增大，0-1转变减小。
四、通过DSC研究了聚合物PF60C10和PF60C12的非等温熔体结晶行为以及PF60C10分子量对非等温结晶和结晶后熔融行为的影响。Ozawa方程和Avrami方程在描述聚合物PF60C10和PF60C12的非等温熔体结晶过程时均有一定的局限性，而用Avrami和Ozawa联合的方法能有效地处理该非等温结晶动力学过程。PF60C10的结晶速率随分子量的增加而增大，PF60C12由于侧链长度增加使其分子链活动性减小，与PF60C10相比其结晶速率减小。另外，分别用Kissinger，Takhor和Augis-Bennett三种模型对PF60C10和PF60C12的非等温结晶活化能进行了估算。PF60C10经非等温结晶后的熔融行为具有明显的预冷速率和分子量依赖性，在一定分子量范围内在其DSC升温曲线上出现双重熔融现象，随着分子量的增大此双重熔融行为逐渐被抑制。
五、通过分子设计并采用Suzuki偶联聚合的方法合成了一系列主链结构刚柔交替的Rod-coil型芴苯聚合物，并对这类聚合物的光物理性能及相转变行为等进行了初步的探索性研究。主链中柔性链段长度的变化对聚合物的光物理性能没有明显的影响，而随主链中共轭链段长度的增加，聚合物光谱向长波移动，氧化电位逐渐增大，还原电位逐渐降低，HOMO-LUMO能隙增大。该Rod-coil型芴苯聚合物玻璃化转变温度随主链中柔性链段比例的增大而减小。聚合物P1(PF6P4P)在较低温度形成一种具有条带织构的液晶相，在DSC曲线的高温区具有典型的双重熔融行为。
Organic polymer materials have attracted much attention in the past decade because of their potential applications in light emitting diodes, field-effect transistors, photovoltaic cells, non-linear optical materials, and electrochromic devices. Among these polymers, fiuorene-based polymers are a kind of most promising blue-light-emitting materials for commercial applications due to their excellent properties such as high photoluminescence (PL) efficiency, good processability and thermal stability. However, much research about polyfluorenes and fluorene-based derivatives is mainly focused on the synthesis of polymers with novel chemical structures, and the investigations on condensed state structure, photophysical properties and their relationship are surprisingly lacking. In fact, it is of great significance to in-depth understand the relationship between condensed state structure and photophysical properties, which can provide more insights into the design of novel optoelectronic polymers as well as the fabrication of high performance devices. In this work, a series of fluorene-benzene based polymers were thus designed and successfully synthesized, and the relationship of molecular structure-condensed state structure-photophysical properties of these polymers were investigated in detail by using various characterization techniques.
1. A series of so-called hairy-rod fluorene-alt-benzene based polymers with different substituted groups on phenylene were synthesized through Suzuki route. The optical properties, fluorescence quantum yields (QY) and electrochemical properties of these polymers were investigated. It was found that the optical properties of the polymers did not show obvious dependence on the alkyl length on phenylene. However, the spectral stability was increased, and the 0-1 transition and the full width at the half-maximum (fwhm) of photoluminescence (PL) spectra was decreased with the increase of the alkoxy length on phenylene. The nature (e.g. electron-donating and electron-withdrawing) of the substituted side groups on phenylene has obvious effect on the optical properties, QY and electrochemical properties of the polymers. Thus, the photophysical properties of the polymers can be tuned by attaching different substituted side groups onto the phenylene. The spectra of the polymers in solutions exhibit dependence on dielectric constants of the solvents used, and the spectra of the polymer solutions shift to longer wavelength with increasing the dielectric constants of the solvents.
2. The thermal stability of the spectra of the polymers was investigated by annealing experiments. A new emission peak located at long wavelength (at about 515 nm) appeared in PL spectra of the unsubstituted polymer (PF6P) films annealed in air, and the intensity of the long wavelength emission increased with the increase of annealing temperature or annealing time. However, the long wavelength emission did not appear in PL spectra of the polymers substituted with alkyl and alkoxy. By comparing the PL spectra of PF6P and the substituted polymers, Fourier-transform infrared (FTIR) Spectroscopy, and PL lifetime measurements have revealed that the long wavelength emission could be attributed to the formation of fluorenone-based excimers. Compared with PF6P, the attachment of alkyl or alkoxyl groups on phenylene effectively inhibits the formation of fluorenone-based excimers and thus remarkably improves the thermal stability of the spectra.
3. Morphology and phase behavior of the polymers substituted with alkyl and alkoxyl groups on phenylene were investigated by differential scanning calorimetry (DSC), X-ray diffraction (XRD) and other techniques. These polymers exhibit typical fibrillar morphology in the films. During heating in DSC, all the polymers substituted with alkoxy on phenylene show a nematic phase. The polymers substituted with hexyl and octyl on phenylene also show a nematic phase, however, the nematic phase disappears for the polymer substituted with decyl. The polymers substituted with alkoxy on phenylene self-organize into a lamellar structure, and their phase behavior shows obvious dependence on the alkoxy length. PF6OC6 shows two crystalline phases; further increasing the length of alkoxy, PF6OC8, PF6OC10 and PF6OC12 only show one crystalline phase. During heating in DSC, PF6OC8 exhibits a melting-recrystallization phenomenon, which is steadily inhibited as the length of alkoxy on phenylene increases. In addition, for the polymers substituted with alkoxy on phenylene, the 0-1 transition in PL spectra of the films decreases with the increase of ordered structure.
4. The nonisothermal crystallization kinetics of PF6OC10 and PF6OC12 was investigated by using differential scanning calorimetry (DSC) under different cooling rates from the melt. It was found that the Ozawa method failed to describe the nonisothermal crystallization behavior of the two polymers. Although the Avrami method did not effectively describe the nonisothermal crystallization kinetics of the two polymers for overall process, it was valid for describing the early stage of crystallization. The combined Avrami-Ozawa method proposed by Liu was able to satisfactorily describe the nonisothermal crystallization behavior of the two polymers. The crystallization activation energies determined by Kissinger, Takhor and Augis-Bennett models were comparable. The melting temperature of PF6OC10 increased with increasing molecular weight. For low molecular weight sample, PF6OC10 showed the characteristic of double melting phenomenon. The interval between the two melting peaks decreased with increasing molecular weight, and only one melting peak was observed for the high molecular weight sample.
5. A series of so-called rod-coil fluorene-benzene based polymers were synthesized through Suzuki coupled polymerization, and the photophysical properties and phase behavior of these polymers were investigated. The photophysical properties of the polymers did not show obvious dependence on the fraction of coil segments in backbone. However, with increasing the fraction of rod segments in backbone, the spectra of the polymers shift to long wavelength and the HOMO-LUMO energy gap increases. The glass transition temperature of the polymers steadily decreases with the increase of the fraction of coil segments in backbone. The polymer (P1(PF6P4P)) shows complex phase behavior, and a strip liquid crystalline texture is observed at low temperature and the typical double melting behavior can be observed at high temperature.
引文
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